Meet Our Team

Jacob Small is the founder and principal attorney of J. Madison PLC, which he formed in 2014. He has counseled and fought for hundreds of employees in employment law matters — in the state and federal courts and government agencies that serve the citizens of the Commonwealth of Virginia, and in federal forums like the EEOC and MSPB that protect workers nationwide. His practice focuses on a broad array of employment law matters, including discrimination, harassment, retaliation, wrongful termination, disability, whistleblower, and wage and hour matters. When the facts and law warrant it, Jacob has been successful on behalf of clients in recovering millions of dollars in settlements and judgments.

Jacob also frequently advises and represents managers and executives in contract negotiations, litigation, arbitration, and other employment-related matters. Not strictly focused on employees facing illegal conduct, Jacob has extensive experience helping employees get the most out of their employment relationships or defend against an angry former employer.

Jacob founded J. Madison PLC in 2014 with a vision for using advanced technology and artificial intelligence to improve the way employment law clients are served, and the beginnings of Cloud Counsel were born. Jacob is a lifelong programmer, having learned to code while in elementary school. He is the sole developer of the Cloud Counsel app offered by J. Madison PLC.

Jacob has presented and spoken frequently at regional and national conferences of practicing attorneys, including for the National Employment Lawyers Association (NELA) and the Metropolitan Washington Employment Lawyers Association (MWELA), and he has written and lectured on legal ethics, courtroom technology, technology in the practice of law, and electronic evidence preservation, storage, and usage at trial. He has also served on MWELA's Board of Directors and its Bench-Bar Committee.

Jacob was early to apply digital forensics methodologies to employment litigation, developing systematic approaches to electronic evidence modeled on those used in criminal investigations. His technical background helps him identify and preserve electronic evidence that is easy to overlook.

Jacob pursues holistic settlements that go beyond monetary compensation. He negotiates for policy reforms, institutional changes, training programs, and accountability measures that protect future employees — seeking to help prevent similar issues from happening again.

Before starting J. Madison PLC, Jacob served in the White House Internship Program during the Obama Administration in the spring of 2012, assigned to the Office of the Vice President, where he supported then-Vice President Joe Biden's counsel's office. He also worked for the Department of Justice and the Commonwealth's Attorney in Loudoun County, Virginia.

Before his legal career, Jacob was a competitive gymnastics coach for seven years, coaching in Virginia and at competitions around the country including at the USAG JO National Championships. The discipline, patience, and ability to break complex skills into manageable progressions that coaching demands directly informs how he manages cases and works with clients.

Jacob is a 2012 graduate of George Mason University School of Law, where he served on the George Mason University Civil Rights Law Journal and Moot Court. He published "Storing Documents in the Cloud: Toward an Evidentiary Privilege Protecting Papers and Effects Stored on the Internet." He was admitted to the Virginia Bar in October 2012. He is also a 2006 graduate of Arkansas State University with a Bachelor of Science in Sports Management.

The name of the firm, 'J. Madison PLC,' holds a special significance for Jacob. 'Madison' is Jacob's middle name, and he shares it with his father David and his late grandfather, James Madison Small.

Jacob and his wife Jenny are parents to three beautiful girls.